MediaSport.id – Juara Liga Eropa 2018/19,Chelsea akan mengawali musim 2019/20 dengan bertandang ke Old Trafford markas Manchester United pada 11 Agustus 2019. Mereka akan melawan Southampton di Boxing Day. Sementara laga penutup dijadwalkan melawan Wolverhampton Wanderers pada 17 Mei di Stamford Bridge.
Berikut adalah jadwal lengkapnya:
*Jadwal masih bisa berubah dikarenakan pengaturan hak siar atau jadwal laga kompetisi lainnya.
| Agustus 2019 |
| 11/8 vs Manchester United (T) |
| 17/8 vs Leicester City (K) |
| 24/8 vs Norwich City (T) |
| 31/8 vs Sheffield United (K) |
| September 2019 |
| 14/9 vs Wolverhampton Wanderers (T) |
| 21/9 vs Liverpool (K) |
| 28/9 vs Brighton and Hove Albion (K |
| Oktober 2019 |
| 5/10 vs Southampton (T) |
| 19/10 vs Newcastle United (K) |
| 26/10 vs Burnley (T) |
| November 2019 |
| 2/11 vs Watford (T) |
| 9/11 vs Crystal Palace (K) |
| 23/11 vs Manchester City (T) |
| 30/11 vs West Ham United (K) |
| Desember 2019 |
| 4/ 12 vs Aston Villa (K) |
| 7/12 vs Everton (T) |
| 14/ 12 vs Bournemouth (K) |
| 21/12 vs Tottenham Hotspur (T) |
| 26/12 vs Southampton (H) |
| 28/12 vs Arsenal (T) |
| Januari 2020 |
| 1/1 vs Brighton and Hove Albion (T) |
| 11/1 vs Burnley (K) |
| 18/1 vs Newcastle United (T) |
| 22/1 vs Arsenal (K) |
| Februari 2020 |
| 1/2 vs Leicester City (T) |
| 8/2 vs Manchester United (K) |
| 22/2 vs Tottenham Hotspur (K) |
| 29/2 vs Bournemouth (T) |
| Maret 2020 |
| 7/3 vs Everton (K) |
| 14/3 vs Aston Villa (T) |
| 21/3 vs Manchester City (K) |
| April 2020 |
| 4/4 vs West Ham United (T) |
| 11/4 vs Watford (K) |
| 18/4 vs Crystal Palace (T) |
| 25/4 vs Sheffield United (T) |